One thing I did notice is that almost everywhere seems to allow pets so that may be something to consider if you haven't yet.

Designing a platform to allow people to interact is not, to me, a useful goal given all the other platforms out there.  

Make sure their deposit and first months rent payment clears before you give them keys or allow them to move in.

Sure, I've got $100 cashflow but I've also got new debt that will only allow me to get one or two more before I have to get "creative." 

We will have approximately $50k cash available when we are planning on buying which, in an area like Boston wouldn’t allow for much.

Here in LA, we're allowed to build studio apartments out of our garages (they're called ADUs).

Like, in Colorado, I believe you're allowed to keep a tenant's deposit in an interest-bearing account, but you couldn't say buy a car with it, obviously.

When my health insurance became $1200/month I got a job as a direct support staff at a group home on 3rd shift which has lasted about 15 years and has always allowed me to have many hours per shift to myself to focus on my real estate and learning things.

Found a local company that allowed 401K/IRA's to be rolled into one of their real estate investment funds.

This allows very fast closings which really appeals to some sellers, they will take fast closing over highest offer if they need to move quickly.2.